


Pretty Hurts

by tebtosca



Category: Supernatural RPF
Genre: Age Difference, Barebacking, Dubious Consent, Gunplay, Light Bondage, M/M, Mobsters, Rimming, Rough Sex
Language: English
Status: Completed
Published: 2013-12-27
Updated: 2013-12-27
Packaged: 2018-01-06 09:45:30
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,326
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1105331
Author URL: https://archiveofourown.org/users/tebtosca/pseuds/tebtosca
Summary: <blockquote class="userstuff">
              <p>Jensen is handed over to a mob boss to pay his father's debts, but someone else in the house might be his key to escaping the life he's trapped in.</p>
            </blockquote>





	Pretty Hurts

**Author's Note:**

  * For [laisserais](https://archiveofourown.org/users/laisserais/gifts).



> Written for laisserais for spn-j2-xmas

Everyone knows that the last thing you want is to get called into Rosey’s office.

Jensen knows that rule better than most, yet here he is with a firm hand on his lower back shoving him through the door without so much as a “good luck, kid.” 

“Mr. Rosenbaum,” Jensen says, gritting his teeth and straightening up to his full, newly growth-spurted height. Despite the whimsical nickname, Rosey is the terrifyingly efficient boss of the East Side, but that doesn’t mean that Jensen has to show him how intimidated he is. Crime lords respect pride, right?

Okay, Jensen might have seen that in a movie, but still.

Rosey sits back in his chair, the leather as spit-shined as the sheen on the crown of his shaved bald head. His posture is lazy, comfortable, like a shark swimming a few practice laps around its prey before going in for the kill.

“Jenny, my boy,” Rosey says with a smirk, and Jensen bristles at that. 

Rosey’s main henchman, Misha, chuckles softly at Jensen’s obvious tension, as he stands steel-rod straight next to his boss. He’s slight for a bodyguard, but the Russians don’t need muscle when they have quick fingers and batshit insanity behind their bright blue eyes.

“How long have you been working for me in this fine establishment?” Rosey continues, waving two fingers around in the air, as if the Gotham Club was something other than a two-bit way station for drunkards looking to cop a feel on bored blondes who know too much.

“Three years, sir,” Jensen replies. 

Three years since his father got in too deep with his gambling addiction and had his legs blown out by men with tattooed faces carrying a tire iron. Three years since Rosey stepped over the broken body and gave his horrified son a chance to pay off the sins of the father. Three years since Jensen quit high school to work in a strip club owned by a mob syndicate. Three years since he’s looked his father in the face.

Three years. Feels like thirty. 

And yet Jensen’s still only nineteen.

“Three years,” Rosey says, letting out a faux-impressed whistle, like this information is news to him. “That’s quite a while, isn’t it Mish?”

“Indeed, boss,” Misha replies, eyes never leaving Jensen’s face.

“Long enough, perhaps.”

Jensen’s heart jumps directly into this throat. The concept of hope burned out of him a hundred Saturday nights ago, but the flicker of it sparks itself in his belly at the possibility.

“Sir?” Jensen says, his voice wavering, that silly pride burying itself under that flicker.

“What if I told you that I have a way for you to pay off all your debts? Your whole family free and clear?” Rosey asks, leaning forward in his chair and resting his chin on his fist. He says it as nonchalantly as he would ordering a pizza, no regard whatsoever to what it could mean for Jensen’s life, his _future._

“That would please me very much, sir,” Jensen says, trying not to show just how eager he is. But his back aches, and the smell of cigar smoke is imprinted on his skin, and he’s just so goddamned tired.

“I thought so,” Rosey says, a little smile working itself over his twisting mouth. 

There’s a pause then, and Jensen remembers that there’s not much Rosey likes better than dramatic effect.

“What would I have to do, sir?” Jensen finally breaks the silence, his fists clenching and unclenching at his side. Misha eyes him carefully, but doesn’t budge from his spot behind the desk.

“I’m having a little trouble with the Irish,” Rosey starts, waving his hand in the air dismissively and rolling his eyes. “JD Morgan is on my ass to cut him into one of my less scrupulous business endeavors, but I’m resisting. As you can imagine, that makes him cranky, and no one likes a cranky Irishman.”

“No one, boss,” Misha agrees, his fingers flexing on the jacket where Jensen is sure his gun rests.

“So, I promised him a little something that might uncrank him, if you get my drift.”

Rosey sits back in his chair again and looks Jensen up and down. Bile rises as suddenly in Jensen’s throat as the flicker of hope is permanently squashed.

“Morgan’s often shown an appreciation for a certain nubile young bar-boy on nights when he feels like vodka over whiskey and comes in to patronize our humble establishment. “ 

He pauses, looking at Jensen with dark, blank eyes. There’s nothing behind them. No pity, no empathy, no soul.

“I’m not a whore,” Jensen spits out, and it’s the very first thing that pops into his mind between _no, please_ and _run, goddamit, run._

“No, of course you’re not,” Rosey replies, clucking his tongue behind his teeth in a tsk. “You’re a businessman, Jensen, just like me. Providing a service that will, in turn, reap benefits for yourself.”

“And my family,” Jensen adds, ashamed that he’s even contemplating this, but knowing he’s going to end up doing whatever it is that he needs to.

“Of course your family.”

“What would I need to do?” 

“Anything Morgan wants you to do.”

Jensen’s entire body tenses before a shudder runs through him.

“Of course,” Rosey continues on, finally something – _viciousness_ —in those bottomless eyes. “If you don’t want to do this for me, I can always call on your sister and see if she’s open to it. What is she now, thirteen? Fourteen? All those blonde ringlets and baby fat, I’m sure Morgan wouldn’t mind too much that she doesn’t have something soft and sweet dangling in between her legs.”

“Don’t you ever talk about my sister like that,” Jensen bursts out, practically snarling and baring his teeth. 

Misha’s gun is pointed at Jensen’s head before he can even take half a step forward.

Rosey snuggles back in his chair, original lazy posture back like clockwork. “So do we have a deal?”

“Do I have a choice?” Jensen chokes out.

“We always have a choice in life, Jensen. You’ve had a choice since you were sixteen. It’s not my fault you still care about other people more than yourself.”

Jensen’s shoulders droop like a marionette with broken strings. All he can do is nod.

“Be grateful I didn’t have problems with the Germans. Huffman would have eaten your spleen for breakfast.”

==

Jensen tells his little sister he’s going on a trip to make a little extra cash for Christmas. She looks up at him with big green eyes and nods solemnly. He’s not fooling her any more than he’s fooling himself, but the lie is important.

He doesn’t bother saying anything to his parents. His father sits in his wheelchair in front of the old bunny-eared television, his eyes not seeing much through the whiskey haze that dulls the pain. His mother is almost as bad, the pill-popping starting years ago when the shame of letting her teenage son take the brunt of the responsibility finally hit her like a tidal wave.

An unmarked black sedan picks him up, a stout guy with a ponytail and black sunglasses leading him towards the backseat. Jensen clutches his lone duffel bag tightly to his chest, holding on to something that is his and his alone.

He can’t help shivering but tries to take deep breaths. He’s not a kid, hasn’t been one in a long time, and he knows that he can handle whatever it is that Morgan deals out to him. Jensen could have run a long time ago, and no one would have blamed him. Hell, if it was just his parents, he would have been on a bus north the second he turned eighteen. But it’s not just his parents, and Jensen will grit his teeth and deal with whatever is coming in order for that little flare of hope to flame again.

The drive lasts about forty minutes, and then Ponytail is ushering him into an impressive looking estate set safely back behind a security gate system that would be worthy of a fortress. Jensen supposes that when you are guys like Rosey or Morgan and have half the town wanting to murder you for your crown, you need the extra security net.

“Mr. Morgan will be with you shortly,” Ponytail says with a grunt, pushing Jensen into what looks like a sitting room. Jensen stumbles a bit before righting himself and looking around the room. The furnishings are dark and weighty, machismo spelled out in the scent of mahogany and leather. 

Jensen tries to take in another breath, but the air is suddenly stifling, like the heat has been cranked up and trapped in the space.

It’s at least a half hour before Morgan shows his face, and by that point sweat is pouring down the sides of Jensen’s face and down his collar, and his eyes are hazy and weary. He can feel the material of his shirt plastering to his back and the carefully styled spikes of his hair wilting. 

Jensen’s mask is melted away before it even gets a chance to be displayed, and if he didn’t feel quite so impotent suddenly, he would beat his fist against the wood-paneled walls in a rage.

“Well, aren’t you a sight,” says a voice from behind him, whiskey-smooth and deep. There is amusement in it already, and Jensen knows for a fact that the heat is very much on purpose.

“It’s a little warm in here,” Jensen replies, turning around and facing the man behind the voice.

Jensen’s seen Morgan in the club before, served him a few times, watched his eyes sweep down Jensen’s body with laser focus. Morgan’s a handsome man, older, mid-forties, with a neat salt-and-pepper beard and roughly knuckled hands. He smiles now, right at Jensen, and if Jensen didn’t know better, it would look almost kind.

“I know what can help,” Morgan says, coming further into the room then. “Strip.”

Jensen does a double take at that, not expecting things to get quite so blatant quite so fast. To make things worse, Morgan is followed in by a giant with too-long hair, sharp cheekbones, and the stance of a killer. The Irish, it seems, do like to keep muscle around.

“That’s alright, I’ll get used to it,” Jensen says, testing the boundaries of the situation and seeing how far he can push things.

Turns out, not far. 

“That wasn’t a suggestion.”

Morgan heads over to the bar and pours himself a few fingers of bourbon in a crystal glass, ignoring Jensen at the same time that he seems very aware of him. Jensen knows that this is the first test, and he sets his shoulders and starts undressing in the most methodical manner possible.

Jensen knows he’s attractive, was even Homecoming king his sophomore year before this whole mess went down. He thinks about bow ties and spiked punch and dancing pretty little Danneel Harris around the gym floor without a care in the world.

Jensen stares straight ahead, avoiding both Morgan’s now pointed focus and the stoic face of his muscle, now leaning against the wall without as much as a twitch. Jensen feels a line of sweat drip down his back, over the curve of the meat of his ass and down his thighs. It tickles, but he schools himself into blankness and waits for Morgan’s inevitable assessment.

“You’re beautiful when you’re all flushed like this.”

Jensen barely holds back an eyeroll.

Morgan’s standing in front of him then, crystal at his lips as he sips the liquor languidly. His eyes are boring into Jensen, taking his flesh apart with sight alone. They’re about the same height, but Jensen has to fight to keep himself from feeling miniscule as Morgan leans forwards and breathes sweet along the curve of his jawbone.

“You’re a little older than what Rosey usually sends me, but I’ve been watching you long enough that I can remember what you were like when the bloom was still fresh,” Morgan whispers directly in his ear, the scent of the booze and his aftershave mixing with the prickle of his beard to make Jensen almost woozy.

Morgan pulls back then, giving Jensen a slight smile, before heading back to the bar to deposit his now-empty glass. 

“He’s got freckles on his dick, Jared. Isn’t that fucking adorable?” Morgan says, gesturing at his bodyguard, who just raises his eyebrows and gives a rather bored nod.

Jensen’s face burns bright red with embarrassment. He does not have freckles on his dick, but of course Morgan is fucking with him for shits and giggles.

“What have you done with this little thing, huh sweetheart?” Morgan says, gruffer now, back in front of Jensen fast as a cobra. One calloused hand is around Jensen’s soft dick, the other cradling his tender sac. Jensen stays as still as he can and looks right into Morgan’s eyes.

“Girls, sir,” Jensen says, as calmly as he can.

“Sir, I like that,” Morgan replies, tugging Jensen’s balls just enough. “I bet you were a heartbreaker, baby. Made all the girls cry.”

“No, sir. I’m a gentleman.”

“I bet you are, sweetheart. “ Morgan’s hand squeezes Jensen’s dick just on the touch side of painful as he chuckles. “Unfortunately for you, present company doesn’t have that particular problem.”

The hand that was cradling his balls comes up and grabs Jensen’s cheeks. He can smell himself, the musk of sweat and testosterone, as Morgan pulls him in for a dirty, ragged kiss. Jensen’s tries to resist, but Morgan’s tongue and the hand around Jensen’s dick brooks no argument, so he relents and allows the man inside. Before long, both hands are holding Jensen’s head, Morgan’s mouth hot and wet and devouring, overwhelming Jensen as he gives into the ride and lets the man take control. 

“Well, look at that,” Morgan purrs, pulling back after a few scorching moments and looking down at Jensen’s bare dick, which is now standing at half-mast where Morgan’s own clothed erection is pressing against it. 

Jensen glances quickly over at the bodyguard, Jared, who is looking at the two of them with an odd look in his eyes. Jensen feels an strange mixture of shame and excitement go through him, and he closes his eyes quickly to try to block both feelings out.

“I’ll make you forget about those high school girls, sweetheart,” Morgan whispers against his mouth, and Jensen is too stunned to figure out how to respond.

==

Morgan doesn’t fuck him that first night.

Jensen spends his first full day at the estate reading books and playing Mario Kart on the game system installed in the room that Jared showed him to. It surprises Jensen, having his own space, but he supposes that Morgan doesn’t need some rented teenager in his way the whole time.

Morgan doesn’t fuck him the second night.

Jensen eats Lucky Charms on the barstool in the kitchen, Jared leaning against the doorframe and watching him. Jensen supposes that Morgan has the guy assigned to make sure Jensen doesn’t steal the silver and make a run for it in the middle of the night. Jared doesn’t talk much, but he smiles when Jensen offers him a spoonful of soggy marshmallows.

Morgan doesn’t fuck him the third night.

Jensen’s feeling off-balance, not knowing anymore what to expect, and he figures that’s exactly the way that Morgan likes it. He’s not used to sloth, having spent the past three years working every single day to provide money for his family. Now he just sits, waits, tries not to get distracted but fails every time. Jared is there the whole time, and Jensen wonders why, but is just lonely enough to appreciate the company.

Morgan does fuck him the fourth night. And fucks him good.

Jensen tries to think about Danneel’s smooth tits as Morgan spreads his ass and puts his hot tongue in places that Jensen never even thought about before. Thoughts of breasts turns to images of Matt Cohen’s thighs in his football uniform, as Morgan’s slick fingers join the unrelenting muscle of his tongue, and Jensen finds himself spreading himself just a little bit more than he thought he would.

It’s surprisingly gentle, or as gentle as it can be with Morgan’s hand on the back of Jensen’s neck and his cock breaking open the ring of Jensen’s virgin ass. The friction of the sheets below rub deliciously against Jensen’s dick, the dick that he can’t even pretend isn’t hard and weeping, and he comes just before Morgan releases inside of him and makes the bed slippery and smelling of sex and shame.

He thinks he can feel Jared’s eyes on him as he creeps down the hall back to his own room a little while later, but he’s not sure. There’s something about the thought of Jared seeing him with Morgan’s fingerprints on his hips and jizz drying on his thighs that makes him hotter than Danneel’s tits and Matt’s thighs put together.

Jensen takes the most scalding shower his skin can bear, then sleeps more soundly than he has in three years.

==

Time becomes a flimsy thing in Jensen’s world. He hasn’t spoken to his family since he entered the front door, doesn’t know much of what’s happening out there beyond these walls. He spends most of his time on-call for Morgan’s whims, going when he’s summoned to be bent over Morgan’s desk or kneel in between his thighs when he’s eating dinner. Morgan likes it when Jared watches, and Jensen finds himself liking it as well, if only because the slow pinking of Jared’s cheeks is the only reaction he gets most of the time.

Jensen knows that this can’t last forever, but he falls into the shambled routine of sex and leisure, getting used to it as surely as someone with Stockholm syndrome gets used to their captivity. 

But Jensen is aware, and that somehow makes things both better _and_ worse.

Things only change three weeks into it when, late one night after Morgan had tied him to the bedposts and fucked him so hard that his knees popped, Jared stops him in the hallway right outside Jensen’s bedroom and presses him against the wall with his thickly muscled body.

Jared takes one of Jensen’s wrists, which are scrapped red and tender from the restraints, and brings it tenderly to his lips. 

“I can get you out of this life,” Jared breathes against Jensen’s mouth before kissing him for the very first time.

And, just like that, Jensen’s world spins on its axis yet again.

==

It had taken only about a week in the beginning before Jensen was fantasizing about Jared while Morgan was shoving his cock down his throat. 

But he’s not thinking of anyone else in the world the first time Jared fucks him in Morgan’s bed.

Morgan’s out of town on business, something to do with the Germans on the South Side, and Jared is babysitting him as usual. It’s been eight full days since their first kiss, since Jared changed his entire world with promises that Jensen is still not sure aren’t just a wet dream haze.

There had been no other real contact in those eight days, keeping the anticipation at a boil that constantly threatens to spill over the pot and land sticky water over the red-hot stove. 

It’s dangerous, this feeling. Wanting something just for himself and not because he’s been told he has to do it or else. And even though there is a part of his brain that knows that he won’t go anywhere unless his sister is included in those promises, he can’t deny that the ache down deep inside of him is lust. 

Lust is exciting. Lust is _new._

Jared confirms with Ponytail that Morgan is a good three hours away, before lifting Jensen up like a ragdoll and throwing him down on Morgan’s all-too-familiar sheets.

Jared crawls up the bed until he is directly over him, his bulk completely blocking the ceiling in a way that narrows everything down to the sensation of the comforting weight of his body. Jared’s pelvis dips down until it brushes Jensen’s, and Jensen can feel the hardness threatening to break through the heavy material of Jared’s expensive dress pants.

Time slows down to a lazy crawl as Jared strips him slowly, exposing him piece by piece. There’s a moment there, when he is completely bare and Jared is still fully dressed, when thoughts of Morgan and the power that he has over him crawls into his skull, but then Jared starts stripping his own clothes off, and it’s okay again. 

Jensen likes to think that Jared can tell what he is thinking, that Jared knows him enough to want to bring him back to this moment between them without the sickness creeping into the edges of his mind. 

_Because this is for me,_ Jensen tells himself, as Jared’s hot-soft-bare skin presses against his own.

As Jared kisses a line straight down from the plushness of Jensen’s lips to the reddish curls around his dick.

As Jared’s fingers trace patterns along Jensen’s belly, connecting the dots between freckles maroon with the blood flushed under Jensen’s skin.

As Jared opens him up with lips and tongue and teeth and then puts him back together again with the length of his cock and his giant hands against the tender flesh of Jensen’s forearms.

“I’ve done a lot of bad things, Jensen,” Jared whispers to him after, as they lay side-by-side on Morgan’s sheets, filthy now with their mingled come and sweat. They’ll have to change them soon, Jensen knows, but the concept of getting out of this blissful state is almost too much to contemplate right now.

“You’re undercover. You did what you had to. I know all about that,” Jensen replies, keeping his voice low as if that will make all the terribleness they’ve seen any better.

Jared hums a little, before lifting one of Jensen’s thighs and sliding right back into the sticky mess he made like he has the right.

Jensen presses back into it, like he has the right as well.

==

The next two weeks are spent planning and fucking, not necessarily in that order. Jared’s handler is going to get Jensen’s sister into Witness Protection, and then Jensen is going to join her. Jared says they have almost enough to bring down Morgan’s entire empire, so it’ll only be a matter of time before that happens and then maybe, just maybe, Jared can join them as well.

Jensen has never felt like this, delirious, gleeful, radiant from the inside out. He kisses Jared like he’s drowning and Jared is the only life raft. Jared holds him against the wall, big hands holding Jensen up, always there, safe and secure. 

Jensen doesn’t know what this is, but thinks, in another lifetime, it could be love.

==

The day that Jared confirms that Jensen’s sister and mother have been safely bundled out of the city, Jensen throws himself at Jared with such gratitude and happiness that it almost knocks the man over. He hasn’t cried since the day the iron destroyed his father’s legs and his future, but he cries now, great weeping trails that spill down his cheeks and down his neck, soaking his shirt and Jared’s suit jacket.

Jared holds him close, kisses his hair, pulls down his pants, opens him up, slides inside, right there on the papers lining Morgan’s desk. Jensen’s cheeks, both sets, are still wet as he moans.

He’s too overcome with pleasure and emotion that he barely notices Jared completely stilling and the sound of a gun cocking.

“What have we here?” Morgan asks, the most mocking of rhetorical questions, as he saunters casually over to where Jared is still balls deep in Jensen’s ass over the mahogany. 

Jensen doesn’t know what to do, trapped on the desk between Jared’s dick and the now vice-like feel of his forearms, which have come up to bracket Jensen’s chest. Jensen’s heart thumps wildly, and all he can tell himself that it’ll be worth it, even if he dies right here, bleeding out on the floor, because his sister is going to get a chance at a real life.

Morgan brings his gun up to Jensen’s face, causing Jensen to flinch on instinct. He trails the gun across his cheekbone and bridge of Jensen’s nose softly, light as a kiss, before pressing the muzzle right past the gate of Jensen’s teeth and into the cavern of his mouth.

Jensen chokes, the flesh of his tongue touching the coolness of the metal, and he wills himself not to panic.

“I have cameras in every room in this house,” Morgan says, leaning forward just enough to push the gun farther back towards Jensen’s throat. His voice has an odd inflection to it that Jensen hasn’t heard before but hopes he never hears again. “And Jared here is my head of security, so he knows that.”

Jensen makes a hurt noise in the back of his throat, which causes him to gag even more around the gun in his mouth. 

That seems to please Morgan, who starts thrusting the gun in and out of Jensen’s mouth in a crude impersonation of fellatio. He chuckles when Jensen starts fighting against it.

“Good thing he knows that I like to watch.”

Jared’s fingers press into Jensen’s flesh and his lips dip down to touch the back of Jensen’s neck. Jensen can’t tell if it’s an apology or victory sign or admission of guilt. He doesn’t think he wants to know.

_I’ve done a lot of bad things, Jensen._

Morgan pulls the gun out and puts the spit-slick thing back in its holster. He runs his thumb along the swollen flesh of Jensen’s lips and leans in for an obscene kiss. Jared’s hips start moving again ever so slowly.

Jensen’s eyes remain dry.


End file.
